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2005
Halogen compounds
Q 0090
Stereoselective Synthesis of (E)-β-Arylvinyl Bromides by Microwave-Induced
of anti-3-Aryl-2,3-dibromopropanoic Acids Using an AgOAc—AcOH
20- 071 Reaction
System. — A new and efficient method for the stereoselective synthesis of
(E)-β-arylvinyl bromides from the corresponding anti-dibromo compounds (I) using an
AgOAc/AcOH system and microwave irradiation is developed. The E-arylvinyl dibromides (II) are prepared in high yields and high stereoselectivities (E/Z >98/2) within
0.5-3.0 min. of reaction time. Microwave irradiation for a shorter time (5s) gives a mixture of the vinyl bromide and the β-lactone [cf. formation of (III)]. Additionally, this
transformation is applied to a one-pot synthesis of (E)-arylvinyl bromide (IIe) in high
yield and high stereoselectivity from the corresponding trans-cinnamic acid. —
(KUANG*, C.; SENBOKU, H.; TOKUDA, M.; Tetrahedron 61 (2005) 3, 637-642;
Div. Mol. Chem., Grad. Sch. Eng., Hokkaido Univ., Sapporo 060, Japan; Eng.) —
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